Elaine’s Boyfriends: The Many Men Who Weren’t Seinfeld (And Him, Too)

Much has been made of Jerry Seinfeld‘s penchant for serial dating on Seinfeld, but Elaine Benes (Julia Louis-Dreyfus) also got in on the action. Over the course of nine seasons, flings were flung, suitors were gossiped about, and one man was judged on whether or not he was “sponge-worthy.”

All told, we saw about thirty of Elaine’s suitors onscreen. What does that tell us? The simple answer would be that Elaine was easy. After all, she was sex positive enough to talk openly about how the scarcity of sponges affected her dating life. However, upon closer examination, it’s more complicated than that. It seems that most of Elaine’s dates were duds, many of the men never got to home base, and that Elaine was perpetually attracted to men suffering from some sort of neuroses.

Elaine was fickle, too. She breezed through men and when they disappointed her, she was able to move on rather quickly. She was obviously more invested in her friendships with Jerry, George, and Kramer than she was with any of these potential soul mates. In fact, we don’t even see her romantically involved onscreen with someone who’s not Jerry until season three. And besides Jerry, her longest relationship is her off-and-on tryst with Puddy.

You learn something else when you look at all of Elaine’s romantic interests: Elaine Benes had game. It’s not just that the President of NBC joined Greenpeace to impress her. Elaine was able to snag a date with John F. Kennedy, Jr. and she went out with MLB star Keith Hernandez. And maybe it’s because she was the lone island of estrogen on a male-driven show, but Elaine was hardly ever hassled for her dating life. The guys didn’t slut-shame her and it was never inferred that she was a failure for being a single, childless woman. She might have been a failure because she actually failed at stuff, but her existence wasn’t defined by her marital status.

As you’ll see by clicking through the gallery below, Elaine might have had many men over the course of Seinfeld, but really, her strongest connection was always with Jerry.

NBC

Jerry SeinfeldActor: Jerry SeinfeldFirst Appearance: S1, "The Seinfeld Chronicles"What’s The Deal With This Guy?: Well, he's the eponymous star of the show. He's a stand up comic, serial dater, and Elaine's best friend. The two are officially broken up when the show starts, but sleep together a few times in early seasons. Many people — including Julia Louis-Dreyfus — think they are soulmates, but are too messed up to get it together. Elaine certainly cares about him far more than the 30 other potential suitors we met on the show...

Photo: NBC

Owen MarchActor: Edward PennFirst Appearance: S3, "The Alternate Side"What’s The Deal With This Guy?: He's a much older writer who suffers a stroke before Elaine can politely break up with him.

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DickActor: David NaughtonFirst Appearance:S3, "The Red Dot"What’s The Deal With This Guy?: Elaine has an office fling with this recovering alcoholic...until Jerry gets him back on the sauce by accident.

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Keith HernandezActor: Keith HernandezFirst Appearance: S3, "The Boyfriend"What’s The Deal With This Guy?: Hernandez is a real-life Major League Baseball player whom Jerry is obsessed with. This causes friction when Elaine starts dating him.

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Dr. RestonActor: Stephen McHattieFirst Appearance: Though he's alluded to earlier, we first see him in S4, "The Pitch"What’s The Deal With This Guy?: He's Elaine's controlling psychiatrist and she needs help wrestling herself from his psychological grasp.

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"Crazy" Joe DavolaActor: Peter CrombieFirst Appearance: S4, "The Pitch"What’s The Deal With This Guy?: He's an unhinged patient of Dr. Reston's and he's obsessed with the idea that Jerry has blocked his way to the big time. Elaine starts dating him by complete accident and is horrified to discover who he is.

Photo: NBC

Russell DalrympleActor: Bob BalabanFirst Appearance: S4, "The Pitch"What’s The Deal With This Guy?: He's the President of NBC. He has one encounter with Elaine and becomes so obsessed with her that he joins Greenpeace to please her (which results in his death).

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John F. Kennedy, Jr.Actor: Never Appeared OnscreenFirst Appearance: S4, "The Contest"What’s The Deal With This Guy?: In the midst of the gang's contest to quit masturbating, Elaine gets a date with JFK, Jr after meeting him at her gym — only to lose out to Marla the Virgin (Jane Leeves) in the end.

Photo: Everett Collection

FredActor: Tony CarlinFirst Appearance: S4, "The Pick"What’s The Deal With This Guy?: He's an ultra-religious guy who gets offended by her accidental nip slip in the company Christmas card photo.

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Jake JarmelActor: Marty RackhamFirst Appearance: S5, "The Sniffing Accountant"What’s The Deal With This Guy?: He's a super-serious author who doesn't like exclamation marks — except he uses them when he's mad at Elaine.

Photo: NBC

Lloyd BraunActor: Peter KeleghanFirst Appearance: S5, "The Non-Fat Yogurt"What’s The Deal With This Guy?: He's a friend of George's — whom his mother is always comparing him to — who eventually suffers a nervous breakdown (and comes back in later seasons played by a different actor).

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Joel RifkinActor: Anthony CistaroFirst Appearance: S5, "The Masseuse"What’s The Deal With This Guy?: He shares a name with a notorious serial killer and the two can't agree on what he should change his name to.

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TonyActor: Dan CorteseFirst Appearance: S5, "The Stall"What’s The Deal With This Guy?: Male bimbo whom Elaine only dates for his looks. George causes him to fall during rock climbing and he is scarred for life. Elaine dumps him because of his ugly face.

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Phil TotolaActor: Mark TymchyshysnFirst Appearance: S5, "The Stand-In"What’s The Deal With This Guy?: They hit it off after being set up by Jerry, but then Phil pulls "it" out too soon.

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AaronActor: Judge ReinholdFirst Appearance: S5, "The Raincoats"What’s The Deal With This Guy?: He's a close talker and very anxious. He causes problems with the gang's parents due to his social anxiety.

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Tim WhatleyActor: Bryan CranstonFirst Appearance: S6, "The Mom and Pop Store"What’s The Deal With This Guy?: She only dates him to find out if he's a re-gifter

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Ned IsakoffActor: Todd KimseyFirst Appearance: S6, "The Race"What’s The Deal With This Guy?: He's a Communist.

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JimmyActor: Anthony StarkeFirst Appearance: S6, "The Jimmy"What’s The Deal With This Guy?: He only refers to himself in the third person, which causes confusion because Elaine thinks another hot guy at the gym is "Jimmy."

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David PuddyActor: Patrick WarburtonFirst Appearance: S6, "The Fusilli Jerry"What’s The Deal With This Guy?: Elaine's longest-lasting and most popular boyfriend after Jerry, Puddy was a dim-witted, sweet mechanic with a deep voice. Elaine was drawn to him for his masculinity. The two were on-and-off for the final few seasons of the show.

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Bob Cobb, aka "The Maestro"Actor: Mark MetcalfFirst Appearance: S7, "The Maestro"What’s The Deal With This Guy?: Orchestra conductor who needs to be called the Maestro. They run off to Tuscany, where they are met by Kramer and Jerry.

John GermaineActor: Jeff YagherFirst Appearance: S7, "The Rye"What’s The Deal With This Guy?: He's a jazz saxophonist, you dig?

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Todd GackActor: John D'AquinoFirst Appearance: S7, "The Calzone"What’s The Deal With This Guy?: He tricks women into dates by losing bets about pop culture trivia. He winds up tricking Elaine, and then Jerry's date into dinner with him.

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David LuknerActor: Cary ElwesFirst Appearance: S7, "The Wait Out"What’s The Deal With This Guy?: George makes a mean comment about his relationship with Beth (Debra Messing) and the two split up. Jerry and Elaine swoop in on them, to no avail.

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KevinActor: Tim DeKayFirst Appearance: S8, "The Soulmate"What’s The Deal With This Guy?: He's a nice guy who turns into "Bizarro Jerry" as soon as Elaine breaks up with him.

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BrettActor: James Patrick StuartFirst Appearance: S8, "The Checks"What’s The Deal With This Guy?: He's obsessed with designer furnature and a specific Eagles song. That would be weird enough, but he is hit in the head with an axe by Jerry, and then dies during surgery when his doctor is distracted by another Eagles song. Talk about dark.

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AlanActor: Tom GallopFirst Appearance: S8, "The Andrea Doria"What’s The Deal With This Guy?: He's really, really bad at breaking up with women.

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Hal KitzmillerActor: Vince GrantFirst Appearance: S8, "The Nap"What’s The Deal With This Guy?: He suffers from terrible back pain and buys Elaine a bed - which offends her because of the implication of sex.

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JackActor: Toby HussFirst Appearance: S9, The Junk MailWhat’s The Deal With This Guy?: He's a cheesy commercial star known as "The Wiz."

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Darryl NelsonActor: Samuel Bliss CooperFirst Appearance: S9, "The Wizard"What’s The Deal With This Guy?: Elaine couldn't tell what race he was. Yeaaahh.... It's even more awkward in retrospect.

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Pinter RanawatActor: Shaun ToubFirst Appearance: S9, The BetrayalWhat’s The Deal With This Guy?: He's a former flame of Elaine's who marries her arch-nemesis, Sue Ellen Mischke. She says they slept together years ago, so he could have ironically come before Jerry on this list.